Can Jon Lester Vest His 2021 Option with the Chicago Cubs?

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Can Jon Lester Vest His 2021 Option with the Chicago Cubs?

Chicago Cubs

Although it was not among the primary concerns of the players and the league as they negotiated terms to play this year, how to handle vesting options and bonuses was certainly an issue that impacted a fair number of players (including Jon Lester). We’ve been waiting on a resolution as the players and the league negotiated this topic in the background and now, per Ken Rosenthal, we have an answer. 

Jon Lester’s six-year contract with the Cubs finishes up this year, but then there’s a team option for 2021 at $25 million ($10 million buyout). It was fairly debatable for the last couple years whether the Cubs would want to pick up that option (it’s only a $15 million decision), but now in the post-COVID environment, it’s extraordinarily likely that the Cubs would not want to commit another $15 million to Lester for 2021. I think contracts are going to be crushed this offseason. 

But that team option is also a vesting player option, whereby if Lester meets certain terms, then he gets to choose whether the option is picked up. 

In Lester’s case, the 2021 option vests as a player option if he hits 400 innings pitched in the regular season between 2019 and 2020 (not going to happen), or if he hits 200 innings pitched in 2020. Well, we know that second one is not going to happen either because of the 60-game season, and that’s why the players and the league have been sorting out how to handle these situations. Hence Rosenthal’s answers above.

So, for Lester’s 2021 option to vest, he’d need to hit the prorated portion of 200 innings for this season – which comes out to 74.1 innings pitched. 

Is that possible? Yes. Is it likely? No. 

In a 60-game season, if Lester is perfectly health and takes the ball every five starts, he will get in 12 starts. That means he’d need to average 6.1 innings per start to get there. Again: possible, but unlikely.

For context, Lester has not hit the 200 inning mark in any of the past three years. Over that time, he’s thrown 534.0 innings over 95 starts, or about 5.2 innings per start. So to get to the vesting option level this year, Lester would have to make every start and also go an average of two outs deeper per start over the course of those 12.

If that weren’t enough of a challenge at age 36, you also have to factor in where Lester is in his ramp-up. On Sunday, he threw 2.1 innings in his first intrasquad game. He’s on pace to make his first regular season start in about two weeks from today, and it’s pretty difficult to see him being stretched out, realistically, to go more than four or five innings out of the gate. So that means, even if he’s ready to roll and pitching well right away, his first few starts are probably going to put him behind the 8-ball. 

All that said, I don’t think you can entirely rule out the possibility that, in this weird and shortened season, Lester is physically able not only to pitch very well, but can also go a little deeper each time out. It’s absolutely possible. It’s just unlikely. An abbreviated start or two, or one mild injury, and that’s that.

Even if Lester’s option doesn’t vest, and even if the Cubs decline the team option as expected, that doesn’t necessarily mean this is the end of the road for Lester and the Cubs. Assuming he wants to keep on pitching after this year, it’s not at all hard to imagine the sides getting together on a new short-term deal. The Cubs could have as many as three on-paper vacancies in their rotation heading into 2021, so a whole lot of pitching will be considered.

(Photo by Jonathan Daniel/Getty Images)

Author: Brett Taylor

Brett Taylor is the Editor and Lead Cubs Writer at Bleacher Nation, and you can find him on Twitter at @BleacherNation and @Brett_A_Taylor.